And they are often blissfully unaware of how much renovations will cost and therefor drive up the price even if the listing is in poor repair.

A better bet though would be buying in a gentrifying area such as West Town, Irving Park or Albany Park which may have stronger upside, you also can get a bit higher cashflow in these areas on condos.

I've had well qualified borrowers not get approved by the lender due to a poor deal, whereas, if the deal is solid as is the borrower, then all is good. 

if your FIL  does not mind  I bet most folks on this site would advise you sell .. 1031 if you canand roll that up to a bigger income producing property. 

Best bet is to have an attorney look over the contract in its entirety so you can get the best advice.

He knew how to do the work but was a poor business owner which showed up as bad money management, among other things.

Also, you can bet I have absolutely jotted down those resources in my collection, thank you! 

Instead of competing with the guy in Nebraska for his $100k deals (disproportionately for broke people with poor credit, especially if they're calling you in California for a mortgage), why not let him have all his $100k deals, and take his California $750k referrals (where >5% down and great credit is more likely anyways)?

Everyone starts with no experience of course and those that have completed deals are a much safer bet than those working on their first. 

And you could refinance into conventional, to free up your VA entitlement... great, so you're "free" to pay another VA funding fee.For your scenario, I'm guessing the best bet would be to leave your VA loan in place, get a HELOC, and boom now you have 20% down, and can once again buy with no PMI, except this time you also will not have that VA funding fee.